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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Steve Robinson# | 30 | 2092-2096 | |
| 2 | Robby Dominguez | 27 | 2055-2058 | |
| 3 | Stan Dowd# | 26 | 2091-2093 | |
| 3 | Kenishi Sakurai# | 26 | 2094-2098 | |
| 5 | Josh Black# | 25 | 2095-2098 | |
| 5 | Curtis Genereux# | 25 | 2094-2096 | |
| 5 | Edgar Gonzales | 25 | 2045-2047 | |
| 8 | Valentin Ceniceros | 23 | 2052-2054 | |
| 9 | Ian Langer# | 22 | 2091-2093 | |
| 9 | Ernie Lockhart# | 22 | 2092-2097 | |
| 9 | Gabe Samz# | 22 | 2088-2090 | |
| 12 | Ricky Aguillon | 21 | 2051-2055 | |
| 12 | Arturo Alba | 21 | 2053-2056 | |
| 14 | Carlos Moran# | 20 | 2092-2094 | |
| 15 | Ron Boone# | 19 | 2094-2095 | |
| 15 | Matt Herzog# | 19 | 2087-2093 | |
| 15 | Victor Luna# | 19 | 2091-2093 | |
| 18 | Raul Esquivel | 18 | 2078-2079 | |
| 18 | D.J. Shipley | 18 | 2050-2051 | |
| 18 | Colton Turner | 18 | 2012-2018 | |
| 21 | Ismael Cintron | 17 | 2060-2066 | |
| 21 | Alex Guzman | 17 | 2040-2041 | |
| 21 | Cruz Loya | 17 | 2070-2072 | |
| 21 | Nick Pelot | 17 | 2065-2066 | |
| 21 | Juan Sanchez | 17 | 2040-2042 | |
| 21 | Matt Tucker# | 17 | 2097-2098 | |
| 21 | Nathaniel Valmont# | 17 | 2097-2098 | |
| 28 | Eric Allard# | 16 | 2094-2096 | |
| 28 | Mike Cavazos | 16 | 2052-2054 | |
| 28 | Vinny Varela | 16 | 2040-2042 | |
| 31 | Chad Kenyon | 15 | 2040-2042 | |
| 31 | Matt Lees | 15 | 2016-2022 | |
| 31 | Danny Montoya# | 15 | 2092-2098 | |
| 31 | Kenny Nieman | 15 | 2082-2084 | |
| 31 | Al Rivera | 15 | 2079-2081 | |
| 31 | Dave Rivera | 15 | 2051-2052 | |
| 31 | Ian White# | 15 | 2094-2096 | |
| 31 | Nick Williams | 15 | 2039-2042 | |
| 39 | Chris Adler | 14 | 2029-2030 | |
| 39 | Sergio Caballero | 14 | 2064-2065 | |
| 39 | Darin Downs | 14 | 2004-2006 | |
| 39 | Assunção Frutuoso# | 14 | 2086-2087 | |
| 39 | Willie Gonzalez | 14 | 2038-2040 | |
| 39 | Jalen Greene# | 14 | 2091-2093 | |
| 39 | Doug Hafner | 14 | 2041-2042 | |
| 39 | Oscar Infante# | 14 | 2090-2091 | |
| 39 | Donald King | 14 | 2053-2055 | |
| 39 | David Klein | 14 | 2055-2059 | |
| 39 | Josh Kline | 14 | 2047-2048 | |
| 39 | Philip Lifenko | 14 | 2052-2055 | |
| 39 | Juan Medina | 14 | 2075-2077 | |
| 39 | Franklin Padilla# | 14 | 2095-2097 | |
| 39 | Nate Reid# | 14 | 2091-2092 | |
| 39 | Jonathan Sharp# | 14 | 2092-2096 | |
| 39 | Isaiah Warren | 14 | 2075-2078 | |
| 56 | Miles Anderson | 13 | 2062-2063 | |
| 56 | Willis Arambula# | 13 | 2097-2098 | |
| 56 | Rich Areizaga | 13 | 2049-2052 | |
| 56 | Todd Aschenbrenner | 13 | 2066-2068 | |
| 56 | Grant Bryan | 13 | 2029-2030 | |
| 56 | Jesus Campos | 13 | 2056-2059 | |
| 56 | Phil Chesser | 13 | 2051-2054 | |
| 56 | Raul Gallegos# | 13 | 2083-2084 | |
| 56 | Randy Hyder# | 13 | 2097-2098 | |
| 56 | Brian Murphy | 13 | 2035-2036 | |
| 56 | Joel O'Brien | 13 | 2055-2058 | |
| 56 | Ryan Ogle# | 13 | 2096-2097 | |
| 56 | C.J. Penney | 13 | 2076-2077 | |
| 56 | Joe Rushing | 13 | 2063-2064 | |
| 56 | Frank Ruvalcaba | 13 | 2055-2056 | |
| 56 | Roger Sanchez# | 13 | 2096-2097 | |
| 56 | Roberto Serrano# | 13 | 2085-2086 | |
| 56 | Wu Situ# | 13 | 2096-2097 | |
| 56 | Josh Stache | 13 | 2053-2054 | |
| 56 | Kevin Van Leeuwen | 13 | 2059-2060 | |
| 56 | Reynaldo Vega | 13 | 2053-2054 | |
| 56 | Eric Wise# | 13 | 2097-2098 | |
| 78 | Andrew Alston | 12 | 2054-2055 | |
| 78 | Kyle Barr | 12 | 2068-2068 | |
| 78 | Bobby Bonilla Jr. | 12 | 2020-2021 | |
| 78 | Patrick Brown | 12 | 2080-2084 | |
| 78 | Alex Bustos | 12 | 2047-2048 | |
| 78 | Juan Canedo# | 12 | 2083-2085 | |
| 78 | Vic Correa# | 12 | 2089-2090 | |
| 78 | Francisco Cruz# | 12 | 2096-2097 | |
| 78 | Marcos Diplan | 12 | 2016-2017 | |
| 78 | Alex Dominguez | 12 | 2049-2051 | |
| 78 | Mike Dougherty# | 12 | 2086-2087 | |
| 78 | Remy Doumani | 12 | 2052-2058 | |
| 78 | Alex Flores# | 12 | 2088-2089 | |
| 78 | Carlos Gil# | 12 | 2094-2096 | |
| 78 | Gary Graham# | 12 | 2093-2094 | |
| 78 | David Halstead# | 12 | 2093-2095 | |
| 78 | Matt Hanson# | 12 | 2094-2098 | |
| 78 | Matt Hart# | 12 | 2094-2098 | |
| 78 | Tatsuhiro Hashimoto | 12 | 2054-2055 | |
| 78 | Pat Holt | 12 | 2059-2060 | |
| 78 | Chance Lennox | 12 | 2054-2055 | |
| 78 | Bob Manfred | 12 | 2065-2066 | |
| 78 | Zack Marchant# | 12 | 2091-2093 |
